What Does Junior Want?

From our May 2005 issue: After Jesse Jackson Jr. spoke out against corruption in the Daley administration, speculation erupted that he was running for mayor. But while city hall may be in his sights, the son of the famous Reverend seems to have other things on his mind

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Jesse Jr. and his siblings have carved out lives both in and out of their father’s long shadow. Here’s what the congressman’s brothers and sisters are up to. 

A former backup singer for Roberta Flack, Santita Jackson, 44, produces her father’s radio show, “Keep Hope Alive,” heard around the country (locally on WGCI–1390 AM).

As a part owner of a lucrative local Anheuser-Busch distributorship (which he owns with his brother Yusef) and as a wide-ranging entrepreneur, Jonathan Jackson, 39, is putting his Northwestern MBA to good use.

The president and majority owner of River North Sales & Service (the beer distributorship he owns with his brother Jonathan), Yusef Jackson, 34, earned a law degree from the University of Virginia and formerly worked at Mayer, Brown & Platt.

Jacqueline Jackson, 29, earned a degree from North Carolina Agricultural and Technical State University, in Greensboro, and is now pursuing graduate studies.

Ever since 1995-when Jesse Louis Jackson Jr. defeated the Daley-backed candidate, state senate minority leader (now senate president) Emil Jones Jr., in the congressional race to replace a discredited Mel Reynolds-the local punditry has regularly speculated about whether Jackson would run for mayor. A few months after Jackson took office, Illinois Issues magazine asked, “Could this guy beat Mayor Richard M. Daley some day?”

But Jackson appeared to have other aspirations, saying during his first campaign that he would like to stick around Congress long enough to become the powerful chairman of the House Ways and Means Committee (à la Dan Rostenkowski) or the first African American Speaker of the House.

The national press took it a step further. “Jesse the Younger appears poised to launch a national political dynasty,” wrote The Los Angeles Times before nominee Jackson had even won the general election. “He’s a hit in Congress,” claimed Newsweek one year into Junior’s congressional career. “Will he be the first black president?”

Jackson is used to this kind of speculation. “All of my life I have had people who have had extremely high expectations of me,” he said in a segment of The History Makers, an oral archive of African American history. “Oftentimes their expectations were higher of me than my own expectations were of myself.”

He seems almost relieved-not jealous, as he’s been depicted in some news reports-that Barack Obama is now the media darling when it comes to the first black president. “[The Obamas] are truly the First Family of our state, and if we keep the faith and keep hope alive,” he told the Chicago Tribune, “they will be the First Family of the United States.”

In the meantime, Jackson is still fighting for his airport, and that is what has really put him so at odds with Daley. For Jackson, the airport is nothing more-or less-than a means to an end: building an economic engine big enough to transform the South Side into a mirror image of the North Side.

Once that’s done, Jackson would like to improve the entire country, beginning with nine amendments to the Constitution that would guarantee the right to health care and a good education, among other things. And then? According to his top aide, Frank Watkins, Jackson sometimes says jokingly, “I want to be on Mount Rushmore.”

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As 2005 began, scandals linked to city hall seemed to monopolize the headlines. Revelations relating to Chicago’s flawed Hired-Truck Program were emerging on a nearly daily basis, while James Duff, a big fundraiser for Mayor Daley, was preparing to plead guilty to 33 counts of fraud and other charges stemming from his assertion that his companies were controlled by women and minorities.

Jackson came out swinging in early January on the radio show “Don Wade & Roma” on WLS-AM. “It is time for people to stand up for good government in the city of Chicago,” Jackson declared. “It is time for people to stand up for fairness.” In a press release a little more than a week later, he placed some of the blame for the scandals in the minority set-aside program on the Chicago city council: “They should be demanding and holding hearings to clean up the stench surrounding Mayor Daley’s affirmative action program.” A few days later, Jackson told reporters: “It’s hard to believe a mayor who is all-knowing and all-powerful in Chicago has no knowledge of what one of his vital programs is doing.”

By that time, other members of the Illinois congressional delegation had reportedly begun discussing whether Jackson was preparing a mayoral run; Jackson insisted he was not. And while Daley didn’t respond to Jackson, several angry aldermen did. “He doesn’t want to be mayor; he wants to be king,” complained Isaac Carothers, a West Side African American alderman who had faced a Jackson-backed challenger in the last election. South Side alderman William Beavers called Jackson a “Johnny-come-lately.” But the black caucuses of the city council, state senate, and state house soon joined forces and called for hearings on the minority contracting program.

About a month later, on a tour of his district, Jackson seems amused-though annoyed-by the whole thing. “All I did was write a press release about affirmative action,” he claims. “I didn’t say anything. Now I’ve become a mayoral candidate!”

Whatever his intentions, though, Jackson didn’t do it lightly. “He’s a master strategist,” says his friend Martin King, the chairman of the board of trustees of Rainbow PUSH (and no relation to the Rev. Dr. Martin Luther King Jr.). “Nothing is done haphazardly or off-the-cuff.”

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We were somewhere near the edge of Peotone when the drugs began to take hold. At least that’s what Rick Bryant, Jackson’s district administrator, tried to pretend when his boss launched into a series of hilarious-and dead-on-imitations of Illinois pols. “That’s off the record!” Bryant interceded from the back seat of Jackson’s congressional-plated black SUV, trying to protect his boss from himself. “That’s the drugs talking!” Jackson was on painkillers for a back he wrenched trying to do some home plumbing-but after the laughter subsided Bryant warned his boss, “Don’t personalize it!”

At times like this, it’s hard not to like Jackson. His round face is almost cherubic, and his body reveals some of the softness of the ex-athlete (though he recently did drop more than 40 pounds). Given his hobbies-hunting, fishing, and model railroading-Jackson could almost pass for a brainy good ol’ boy.

Jackson’s district tour, which he has been giving to reporters for years, is equal parts public policy seminar, history lesson, standup comedy routine, and buddy road trip. Throughout, he is relentlessly on message, having repeated the same shtick for ten years both out loud and in his writings.

The tour had convened at Jackson’s South Shore home, a modest brick affair near the South Shore Cultural Center and about 100 yards from Lake Michigan. It is a cozy home with humble furnishings, but the truth is that Jackson has essentially moved his family-his 42-year-old wife, Sandi (a lawyer), and his two kids, Jessica, five, and two-year-old Jesse III-to a home in Dupont Circle in Washington, D.C.

The South Shore house, though, is hardly devoid of life. Upon entering the basement, Jackson announced, “This is ‘Jackson for Congress!’” And there, crammed amid scattered pieces of weightlifting equipment and a washer and dryer, was a campaign war room: computers, an insert mailer, paper folding machines, a post-card machine, and three television screens, each tuned to a different network.

Jackson, a stickler for organization in a way his father never has been, is credited with bringing modern technology to the Rainbow Coalition while he worked there as national field director. He bought the same computer system, able to catalog reams of demographic and voting information about his would-be constituents, for his first campaign. Jackson has also run the campaigns of other South Side politicians out of his basement-including those of state senator James Meeks and state representatives David Miller and William Davis. His team, says Jackson, has won 13 elections without a loss.

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